878 J. Chin. Chem. Soc., Vol. 56, No. 5, 2009
Hsu et al.
(m, 2H, CH2CH3), 0.95 (t, J = 7.5 Hz, 3H, CH2CH3); 13
C
Colourless liquid; 1H NMR (300 MHz, CDCl3): d 7.71 (d, J
= 16.2 Hz, 1H, ArCH), 7.64 (d, J = 7.8 Hz, 2H, Ar), 7.59 (d,
J = 7.8 Hz, 2H, Ar), 6.51 (d, J = 16.2 Hz, 1H, CHCO2Bu),
4.23 (t, J = 6.6 Hz, 2H, CO2CH2CH2), 1.73-1.65 (m, 2H,
CO2CH2CH2), 1.48-1.41 (m, 2H, CH2CH3), 0.97 (t, J = 7.5
Hz, 3H, CH2CH3); 13C NMR (75 MHz, CDCl3): d 166.3,
142.4, 137.7, 131.3, 127.9, 125.6, 121.8, 120.7, 64.5, 30.5,
19.0, 13.5.
NMR (75 MHz, CDCl3): d 166.9, 144.2, 140.2, 131.5,
129.3, 127.8, 116.9, 64.0, 30.6, 21.1, 19.0, 13.5.
2-Methyl-trans-cinnamic acid n-butyl ester (3d)6
4-Butyl-trans-cinnamic acid n-butyl ester (3h)9
Pale yellow liquid; 1H NMR (400 MHz, CDCl3): d 7.97 (d,
J = 15.9 Hz, 1H, ArCH), 7.54-7.52 (m, 1H, Ar), 7.27-7.16
(m, 3H, Ar), 6.35 (d, J = 15.9 Hz, 1H, CHCO2Bu), 4.21 (t, J
= 6.7 Hz, 2H, CO2CH2CH2), 2.42 (s, 3H, ArCH3),
1.72-1.65 (m, 2H, CO2CH2CH2), 1.48-1.39 (m, 2H,
CH2CH3), 0.96 (t, J = 7.4 Hz, 3H, CH2CH3); 13C NMR (100
MHz, CDCl3): d 167.0, 142.1, 137.5, 133.3, 130.6, 129.8,
126.3, 126.2, 119.2, 64.3, 30.7, 19.6, 19.1, 13.6.
Pale yellow liquid; 1H NMR (300 MHz, CDCl3): d 7.69 (d,
J = 16.2 Hz, 1H, ArCH), 7.46 (d, J = 7.8 Hz, 2H, Ar), 7.20
(d, J =7.8 Hz, 2H, Ar), 6.43 (d, J = 16.2 Hz, 1H,
CHCO2Bu), 4.23 (t, J = 6.6 Hz, 2H, CO2CH2CH2), 2.64 (t,
2H, ArCH2), 1.74-1.60 (m, 4H, CO2CH2CH2), 1.50-1.34
4-Acetyl-trans-cinnamic acid n-butyl ester (3e)7
(m, 4H, CH2CH3), 0.97 (t, J = 7.5 Hz, 3H, CH2CH3); 13
C
NMR (75 MHz, CDCl3): d 167.1, 145.4, 144.4, 131.8,
128.8, 127.9, 117.0, 64.1, 35.4, 33.2, 30.7, 22.2, 19.1, 13.8,
13.6.
Pale yellow liquid; 1H NMR (300 MHz, CDCl3): d 7.96 (d,
J = 8.1 Hz, 1H, ArCH), 7.68 (d, J = 16.2 Hz, 2H, Ar), 7.60
(d, J = 8.4 Hz, 2H, Ar), 6.53 (d, J = 16.2 Hz, 1H,
CHCO2Bu), 4.22 (t, J = 6.6 Hz, 2H, CO2CH2CH2), 2.61 (s,
3H, COCH3), 1.75-1.65 (m, 2H, CO2CH2CH2), 1.51-1.38
2-Methoxy-trans-cinnamic acid n-butyl ester (3i)5
(m, 2H, CH2CH3), 0.97 (t, J = 7.5 Hz, 3H, CH2CH3); 13
C
Pale yellow liquid; 1H NMR (300 MHz, CDCl3): d 7.99 (d,
J = 16.2 Hz, 1H, ArCH), 7.51-7.48 (m, 1H, Ar), 7.35-7.30
(m, 1H, Ar), 6.97-6.88 (m, 2H, Ar), 6.53 (d, J = 15.9 Hz,
1H, CHCO2Bu), 4.20 (t, J = 6.6 Hz, 2H, CO2CH2CH2),
3.81 (s, 3H, ArOCH3), 1.73-1.64 (m, 2H, CO2CH2CH2),
1.47-1.39 (m, 2H, CH2CH3), 0.96 (t, J = 7.4 Hz, 3H,
CH2CH3); 13C NMR (75 MHz, CDCl3): d 167.5, 158.2,
139.8, 131.3, 128.7, 123.3, 120.5, 118.6, 111.0, 64.1, 55.3,
30.7, 19.1, 13.6.
NMR (75 MHz, CDCl3): d 197.1, 166.4, 142.8, 138.6,
137.8, 128.7, 128.0, 120.6, 64.5, 30.6, 26.5, 19.0, 13.6.
Trans-4-fluoro-cinnamic acid n-butyl ester (3f)8
Pale yellow liquid; 1H NMR (300 MHz, CDCl3): d 7.63 (d,
J = 16.0 Hz, 1H, ArCH), 7.50 (dd, J = 8.6, 5.4 Hz, 2H, Ar),
7.05 (d, J = 8.6 Hz, 2H, Ar), 6.35 (d, J = 16.0 Hz, 1H,
CHCO2Bu), 4.20 (t, J = 6.7 Hz, 2H, CO2CH2CH2), 1.71-
1.63 (m, 2H, CO2CH2CH2), 1.47-1.39 (m, 2H, CH2CH3),
0.96 (t, J = 7.5 Hz, 3H, CH2CH3); 13C NMR (75 MHz,
CDCl3): d 166.0 (d, J = 103.3 Hz), 162.0, 143.0, 130.6,
129.7, 106.0 (d, J = 21.8 Hz), 64.3, 30.6, 19.0, 13.6.
4-Trifluormethyl-trans-cinnamic acid n-butyl ester
(3g)6
3-Nitro-trans-cinnamic acid n-butyl ester (3j)10
White solid, mp = 63-65 °C; 1H NMR (300 MHz, CDCl3): d
8.21 (d, J = 16.2 Hz, 2H, Ar), 7.70 (d, J = 16.2 Hz, 1H,
ArCH), 7.62 (d, J = 16.2 Hz, 2H, Ar), 6.57 (d, J = 15.9 Hz,
1H, CHCO2Bu), 4.23 (t, J = 6.6 Hz, 2H, CO2CH2CH2),